Helv. Chim. Acta 1980, 63(8), 2264-2270 teaches electrically neutral lipophilic di-, tri- and tetra-amides containing tertiary amine nitrogen atoms as ligands in polymeric membranes.
U.S. Pat. No. 2,746,901 relates to salts of alpha-di-alkylamino-N,N-di-alkyl acetamides for treating dysmenorrhea.
U.S. Pat. No. 2,256,186 teaches quaternary nitrogen compounds prepared by causing a halogencarboxylic acid amide to act upon a disubstituted aminoacylamide obtainable by reaction of halogenacylamides with secondary amines. The use of the quaternary compounds are as softeners for textiles and as agents for the improvement of the fastness qualities of substantive dyeings.
JP47004941 teaches ethylenediamine tetra(N,N-dialkylacetamide) compounds as heat stabilizers for acrylic fibers. Alkyl is ethyl or butyl.
JP45037547 teaches ethylenediamine tetra(N,N-dialkylacetamide) compounds as additives in acrylic fibers. Alkyl is C1-C4.
U.S. Pat. No. 4,801,618 discloses ethylenediamine tetra(N,N-dialkylacetamide) compounds for improving feed utilization and lactation in ruminant animals. Alkyl is straight or branched chain of one to six carbon atoms.
U.S. Pat. No. 3,214,377 discloses phenylamides of organoamine polyacetic acids as antioxidants for lubricating oils. The preferred antioxidant is ethylenediamine tetra(N-benzylacetamide).
EP835924 relates to the use of carboxylic acids, metal salts of carboxylic acids, amine salts of carboxylic acids and carboxylic acid amides as lubricating oil additives.
U.S. Pat. Nos. 2,830,019 and 3,449,097 disclose hydrocarbon oil compositions containing an additive which is the salt of an amine and an amino-carboxylic acid.
U.S. Pat. No. 4,249,912 teaches aminoamide detergent additives for fuels.
U.S. Pat. No. 2,954,342 teaches certain amides of ethylenediaminetetraacetic acid as antioxidants for lubricating oils.
U.S. Pat. No. 3,173,770 relates to certain amides of ethylenediaminetetraacetic acid as metal deactivators for fuels.
U.S. Pat. Nos. 3,202,491 and 3,407,051 relate to fuel oils that contain imide-amide reaction products of ethylenediaminetetraacetic acid and primary amines.
U.S. Pat. No. 3,024,277 as well teaches certain amides of ethylenediaminetetraacetic acid as antioxidants for lubricants.
U.S. Pat. No. 4,242,101 discloses the use of imides or amide-imides which are the reaction products of nitrilotriacetic acid or of ethylenediaminetetraacetic acid with amines in fuels for gasoline engines.
U.S. Pat. Nos. 5,282,872 and 5,071,445 disclose amide, amide/ammonium salt or ammonium salt compounds of an aminoalkylene polycarboxylic acid and a secondary fatty amine as additives in fuels.
U.S. Pat. No. 5,376,155 teaches the reaction products of aminoalkylenecarboxylic acids with primary or secondary amines as paraffin dispersants in mineral oils.
It has now been found that certain N-alkylaminoacetamide or alkylenedi-, alkylenetri- or alkylenetetra-amine acetamide compounds are excellent antiwear and friction modifying additives for lubricating oils.